Irene Izzo

Chemoselective Aldehyde and Imine Reduction by a Macrocyclic Triazole–Borane Complex Triggered by a Non‐innocent Proton–Hydride Interaction

Luca Di Marino, Artur Brotons Rufes, Rosaria Schettini, Giorgio Della Sala et autres

Borane complexes have long been recognized as efficient reducing agents. Among them, amine–borane complexes display a broad range of stability and reactivity, making them attractive for both laboratory and industrial applications. In this contribution, we report the reduction properties of a thermally …

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Toward the Valorization of Cotton Wastes: Application of a Gossypol‐Derived Ligand to an Asymmetric Diels–Alder Reaction

Gianluca Montella, Yassine Benhamidat, Francesco De Riccardis, Irene Izzo et autres

ABSTRACT Gossypol, a major metabolite of cotton plants, has been used for the first time as a source material for the preparation of derivatives employed in asymmetric catalysis. Specifically, the (R)‐enantiomer of the 6,6’,7,7’‐O‐tetramethyl derivative of apogossypol has been synthesized in five …

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Cyclic α‐/β‐Peptoids: Bioinspired Macrocyclic Peptidomimetics

Irene Izzo, Assunta D’Amato, Giovanni Pierri, Francesco De Riccardis

Abstract Peptoid‐based macrocycles represent precious tools in biomimetic and supramolecular chemistry for their innate propensity to recognize biopolymers, molecules, and ion guests, and also for their impressive ability to adopt stable secondary structures and display remarkable chemical diversity. The ample variety of …

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Bis-thiourea and macrocyclic polyamines as binary organocatalysts for the ROP of lactide

Assunta D’Amato, Maria Voccia, Filippo Bruno, Sara D’Aniello et autres

New binary catalysts formed by a bis-thiourea and a series of flexible polyaza-macrocycles are revealed to be efficient catalysts for the ring opening polymerization (ROP) of l -lactide.

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The peptoid's path to understand the role of CH...OC and CO...CO interactions in proteins

Consiglia Tedesco, Giovanni Pierri, Nancy D’Arminio, Rosaria Schettini et autres

Flexible and Convergent Enantioselective Total Synthesis of ( R )-Juglanaloids A and B: Two Phthalide Spiro Alkaloids with Potential Alzheimer’s Disease Inhibitory Activity

Ibrahim Khettar, Arianna Sinibaldi, Rosaria Schettini, Giorgio Gorini et autres

Juglanaloids A and B are recently isolated natural products characterized by an unprecedented spiro bicyclic isobenzofuranone-tetrahydrobenzazepinone framework and a promising antiamyloid activity. Here reported is a straightforward convergent total synthesis of these natural products, which were obtained in high enantiomeric purity (94% …

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1,2,3‐Triazole‐Containing Azamacrocycles from Chiral Triazolopeptoids: Synthesis and Solid‐State Studies

Alicja Malgorzata Araszczuk, Giovanni Pierri, Rosaria Schettini, Chiara Costabile et autres

Abstract Two new chiral 1,2,3‐triazole‐containing macrocyclic oligoamides ( i. e .: triazolopeptoid 4 and 5 ) were obtained through solid‐phase synthesis of linear precursors followed by high dilution macrocyclization reaction. Theoretical (DFT) and spectroscopic (NMR) studies revealed the intricate interplay between the …

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An Access to Chiral Phthalides: Enantioselective Synthesis of Escitalopram

Rosaria Schettini, Antonella Dentoni Litta, Arianna Sinibaldi, Assunta D’Amato et autres

Abstract A method for the asymmetric synthesis of phthalides containing a stereogenic γ‐carbon has been described. The protocol, based on the arylogous Michael addition to chiral alkenoyl oxazolidinones catalyzed by a crown ether under phase‐transfer conditions does not require anhydrous conditions and …

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Deconstructing Best‐in‐Class Neoglycoclusters as a Tool for Dissecting Key Multivalent Processes in Glycosidase Inhibition

Yan Liang, Rosaria Schettini, Nicolas Kern, Luca Manciocchi et autres

Multivalency represents an appealing option to modulate selectivity in enzyme inhibition and transform moderate glycosidase inhibitors into highly potent ones. The rational design of multivalent inhibitors is however challenging because global affinity enhancement relies on several interconnected local mechanistic events, whose relative …

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Dissecting Key Multivalent Processes in Glycosidase Inhibition: Insights from Thermodynamic Modelling and Atomistic Simulations

Martin Spichty, Yan Liang, Rosaria Schettini, Irene Izzo et autres

Abstract Multivalency represents a powerful approach to increase the inhibition potency of moderate glycosidase inhibitors. Regarding the key role of catalytic glycoside hydrolysis in biology, understanding the molecular mechanisms and origin of the multivalent inhibitory effect is of great interest and presents …

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Cyclic peptoids as building blocks for engineering porous molecular solids

Giovanni Pierri, Irene Izzo, Francesco De Riccardis, Consiglia Tedesco

Porous materials received a lot of attention in recent years due to their peculiar features and potential applications in a variety of fields ranging from gas storage to green chemistry. Porous molecular crystals, in which molecular units are kept together by weak …

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The Antimicrobial, Antibiofilm and Anti-Inflammatory Activities of P13#1, a Cathelicidin-like Achiral Peptoid

Valeria Cafaro, Andrea Bosso, Ilaria Di Nardo, Assunta D’Amato et autres

Cationic antimicrobial peptides (CAMPs) are powerful molecules with antimicrobial, antibiofilm and endotoxin-scavenging activities. These properties make CAMPs very attractive drugs in the face of the rapid increase in multidrug-resistant (MDR) pathogens, but they are limited by their susceptibility to proteolytic degradation. An …

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